VR: Virtual Reconnecting
by Wanderlust315
Summary: Slight AU. Jess and Rory went to Chilton together and became best friends. Although they both clearly had a crush on each other, they never pursued anything. Until Rory's stress turns into a common sexting habit between the two. What will happen when they see each other again in person after four years? Twoshot!


**A/N: Hey all! I've loved Gilmore Girls for YEARS and particularly Literati, but this is only my first fanfic for them. There's definitely going to be a part two (which was actually what I intended to write before this happened), so I hope you enjoy.**

**Disclaimer: I don't own anything. I'm a college student. **

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After a long day of courses, Rory reached to her phone for some stress relief. At first, she threw on some music as she showered the day off. While the hot water and steam started, it still wasn't quite right. So she grabbed a book and laid in bed, reading. That didn't help much either though, because her thoughts kept drifting. So after a half hour, she gave in to the stress relief she really wanted.

Her hands trailed lightly down her body, stopping briefly to pinch and twist her nipples. She arched her back a bit as she ached for more. One hand stayed on a breast as the other teased its way down. She rubbed her stomach, fingers tickling their way further down, just barely touching the hair below. She massaged the area, before firmly putting her hand down further. With another pinch on her nipple, she slid a finger feeling her wet folds. Rory let out a small sigh of relief, but when she went to play with her hole, she found she wasn't comfortably wet enough.

Frustration started to make its way through her body, but she tried to shake it off as her finger traveled back up just the tiniest bit to find that bundle of nerves. She circled it, teasing herself, trying to build anticipation. Instead, she found it just let her thoughts drift off. Skipping the teasing, she dove in and started rubbing it in circles under her finger. As her back arched again, she grabbed her breast, loving how it felt under her hand. Until she started thinking about the lecture she had had earlier in the day. Stubbornly, she persisted with her actions, trying to block out all the stress and only feel pleasure.

She hadn't gotten some in so long. She was horny. It almost felt like she was always horny. Hell, sometimes when Lucy teased her, she felt herself blush some. Lucy just loved that. Lucy was also frequently the one who pointed out that she needed to get some.

Great, now she was thinking about Lucy as she masturbated. Her hands came to a rest over her breast and mound as Rory finally realized her actions had become mechanical and not-at-all pleasurable.

However she had succeeded in making herself hornier somehow. She wanted to get off now. She needed it. Fuck, she deserved it. She could have gotten laid many times. She wasn't unattractive. She just never made time to go to the bar. Or cared to flirt with any guys from her class. She was all work and no play _all the time._ Usually, she didn't mind. Tonight? It was taking its toll.

Of course she had a solution for nights like these. All it would take are a few taps, assuming he was still up. He would be more than happy to help. She _knew _that.

But they normally didn't just text each other for the sole purpose of sexting. Usually they had already been messaging for some time. Maybe talking throughout the whole day or even consistently over the span of a couple of days. Then evening would come and they'd be going back and forth as quick as a normal conversation. The flirting was always there between them, but it would heat up in the evening. Then it would get steamy. Eventually, one of them bit the bullet and said something that let the other decide to jump.

Or so it seemed. Rory would never admit to him that when she was feeling like this, and either chickened out of texting him or he had fallen asleep, that she would take nudes to send to him when they later did end up sexting. Planned nudes were always easier. . . and looked so much better. She wouldn't admit it, but she liked taking the time to shave and dress up for him to see at a later date. She loved positioning her body just right to cover all the NSFW parts but still leaving plenty to the imagination. She loved taking pictures that showed just how turned on she was thinking about him, fantasizing. The way her face scrunched in pleasure, or how her mouth looked all red, wet, and plump from biting her lip to hold back her moans.

She knew she was hot. So did he. He never shied away from telling her so either. I guess that was a benefit of knowing each other for so long. It never felt uncomfortable between them. Maybe it should have. They certainly never did this in high school. In high school, it was all so. . . chaste, looking back. Back then, the hottest thing was holding eye contact for a few seconds longer than necessary after a few flirty remarks. But they had been best friends and too scared to ruin anything, making the assumption they had all the time in the world together.

She really shouldn't have been so surprised, she thought as a hand trailed its way down to her now-slick folds, playing with herself again. He hated being at a fancy private school in the suburbs. Even though a uniform looked damn good on him.

That certainly was something she could never deny. Not even in high school. He was incredibly hot. He definitely made the most of it. She could feel her panties getting wetter as she played with both her nipples.

So off he went to New York City, while she stayed in Connecticut with a full-ride to a good college. She spent most of their summer away abroad, so they hardly saw each other. When they did, it was with all their friends. At that point, it was hard to tell what was flirting and what was just them. What was sexy and what was nostalgic. When he put his arm around her or kissed her cheek, she leaned into it, too afraid it would be the last.

Then the texting started. They took a month or two simply adjusting to their new lives, new normal, but as soon as things settled, they were back in regular contact. It was innocent enough to start, catching up with one another. Silly selfies. _Drunken_ selfies. At this thought, Rory scrolled through her photos searching for a particularly hot screenshot of him from a while back, shirtless. When she found it, she moaned in relief as a finger plunged into her very wet hole.

Yeah, then it became not-so-innocent. Finals came around and Rory got more stressed. She stayed up later. Of course, he knew all of this, because he knew her _so well. _He stayed up later, even though he had work early the next morning, just to make sure she had whatever she needed. A virtual shoulder to cry on? Check. A study buddy? Done. But after watching her work so hard, he chose to use his discretion and determined what she needed. And okay, maybe he needed it too, because he hadn't gotten laid in a long while either. And maybe that was due to a certain high school friend he was texting rather frequently.

Rory had her hesitations at first. She was nervous and anxious, not at all familiar with this. But after that first orgasm he gave her simply from descriptions of what he wanted to do to her, it was fair game, she recalled as she moved her fingers in and out of herself faster.

Nowadays, as Rory came closer to graduation and he was enrolled part-time in college and working full-time, there was less time for texting. Daily texts were more like weekly. Which was totally okay, fine. It just meant that Rory didn't get as much. . . stress relief as she was used to.

Rory groaned, frustrated. This wasn't working. Yes, now she was wetter, but she couldn't get herself off. She found she couldn't anymore without him. Even after that cheeky gifted vibrartor her mom got her a couple months ago.

Rory turned to her phone, convinced to text him. Instead, she opened up a private browser and started searching for porn. It wasn't her favorite way to get off, but she'd give it a go.

Hardly a minute into the first video, the browser was closed. Nope. Actually turning her off, which was the last thing she wanted.

With a deep breath, she opened his messages. Instead of texting him, she scrolled up. Okay, yes she was a chicken, and yes, she did save his dirty messages, but can you blame her when they are as hot as:

_I want to spend today with my head buried between your legs, lapping you up all day until you can't speak or think anymore. _

_I want to feel the way your thighs squeeze my head, forcing me to stay there._

_I'm going to bite on those pretty nipples of yours, sweetheart. _

_Just wait until I get my hands on that ass. _

_What a good girl, taking all of my cock like a slut. _

And her favorite?

_Fuck, Ror, I'm cumming. Cumming for you._

At this point she was moaning with a hand gripping her breast almost painfully. Her breaths were coming fast and hard as her fingers played with her clit. She kept reading his messages, but still found she couldn't cum. And she wanted to so badly.

R: _Hey Jess_

She sent off the message with a few easy, unthinking taps. It was eleven at night. Prime booty call hours. She was done caring. It's not like she hadn't made the first move before, she thought to herself. _I've just never texted him for solely this purpose, _she reminded herself stubbornly.

After a few minutes, mindlessly playing with herself still, her phone chimed.

J: _Hey Rory! How are you?_

Rory bit her lip, feeling almost-guilty. _Does he even suspect anything? Is it bad that I'm texting him for sex?_

After a couple seconds, she decided to indulge the small talk but maintain some honesty.

R: _Not much. Just laying in bed after a long day. What about you?_

Ah, a classic opening. And also the truth. Sort of.

J: _Ha, the same_

. . . Not much of an opening, she thought. Another chime.

J: _Why a long day?_

Her response was quick. _Everything is constantly about graduation. Paris has this whole plan. Every hour of the day is accounted for basically._

So was his. _Yikes. Classic Paris though. Dunno what else you expected after living with her for four years. Totally crazy._

R: _Yeah, maybe not my best move. Causes more stress than anything. _

She bit her lip, knowing that word would likely bring his thoughts to dirtier places.

J: _Hmm. You've been stressed a lot lately. Anything I can do to help?_

In true Jess fashion once he realized what she wanted, he cut right to the chase. She let out a small whimper.

R: _It seems I can't get off all that easily without your. . . encouragement anymore._

J: _Yeah, sweetheart? You've been playing with yourself, thinking about me?_

Rory's moan was low and breathy as she typed out her response.

R: _Yea, I'm so wet. So wet for you Jess. I've been laying here with fingers pumping in and out of me reading through our messages. Getting more and more turned on and wet._

J: _Fuck, Rory. That's hot as fuck. Do you do that often, baby?_

Rory's lip hurt from how hard she was biting it.

R: _More often than I'd like to admit._

J: _Tell me. _

Rory groaned in pleasure at how demanding he was.

R: _Usually once a day. Sometimes more. Recently, a lot more._

J: _Yeah? Which parts do you like re-reading?_

R: _I like it when you call me a slut. . . or when you call me your good girl. I love it when you're rough and demanding. When you want me to please you. The way you respond when I send you pictures. _

J: _Christ, I'm so fucking hard. Who would have guessed you'd be so dirty, Gilmore?_

Rory smiled and her response came easily. _Clearly you did. You started this._

J: _I never dreamed I'd be so lucky. Now why don't you send me a picture of those tits I love to imagine kissing, nipping, and sucking so much?_

R: _Yes sir ;) _

This time Jess's response took a minute or two. Much longer than normal. Instead of choosing to send a posed one, she took one in real time. In it he could see the bottom half of her face, her lip between her teeth, then a hand squeezing a breast with the other trailing down to a place he knew but couldn't see. Her nipples were clearly hard. The addition of calling him sir was the cherry on top.

J: _You're such a tease sometimes. I oughta tie those hands above your head and force you to beg me for my cock. _

R: _Believe me, you don't have to force me. I'm so fucking horny. Please Jess, please. Show me your dick. I want it._

She knew whining would get her what she wanted. Within seconds, a picture of his dick loaded on her screen. She clicked it to have it take up the whole screen. He was standing in front of the mirror in his boxers, very clearly tented. His hand covered some of it, clearly massaging his dick. Before she could respond, another message from him had already arrived.

J: _A good girl gets to see my dick. A needy little whore has to give me more. _

Rory loved it when he punished her. Mimicking him, she got down on the floor on her knees in front of her mirror and took a picture with her legs spread and tits out.

R: _Imagine me like this in front of you with your cock in my mouth. I'd play with myself as I look up at you, making eye contact, and then sucking harder. Eventually some drool would make it down my face, maybe I'd gag on your dick. Mmm. _

J: _Now there's my good girl. I'd tangle my fingers in your hair as I thrust into your mouth, making you deep throat it and gag on it. I'd keep pumping it in and out of you._

Still sitting in front of the mirror, Rory spread her legs more and started fingering herself again. Quickly, she took a picture so he could see what she was doing.

R: _All for you. Please keep going._

J: _Mmm, yeah that's right, doll. Imagine my dick in your mouth and keep playing with yourself. I'd take my cock out and slap you on each cheek with it. Then I'd force you to open your mouth as I tapped it against your lips, teasing you. You need it, don't you, slut?_

R: _Yes! Please, sir, your slut needs it. Your slut needs your cock. _

J: _Good girl. I'm stroking it. It's so hard. Wish your lips were around it. I'd fucking cum all over that pretty face of yours. _

As Rory started tapping out her response, a new image appeared in her messages. She opened it to see it better and let out a long moan as she stared at Jess' long, thick cock. She wished. . . She stopped thinking and started typing.

R: _I wish I could worship your cock. I want to trace over each vein with my tongue and kiss the tip of it before bobbing my head up and down it, taking it all in my mouth. You can cum in my mouth. On my face. Please, I just want your cock._

J: _Mm, oh fuck, baby. You'd let me cover that face in cum? Your hair?_

R: _Whatever you want as long as I get to cum. And you rinse it out of my hair in the shower ;)_

J: _Done deal. I'd love to see your boobs soapy and wet. _

R: _Well, I may or may not have a picture like that saved for you. . . _

J: _Stop touching yourself until you send that to me._

J: _I mean it, Ror. You're not allowed. I won't let you watch me cum. _

The threat had her sending it without hesitation.

J: _Mmm god you're so sexy. _

R: _That was mean, and you know it._

J: _Want me to make it up to you? Answer my call._

Just as soon as Rory had finished reading his text, his call was coming through. She hesitated briefly. They'd never done this before. Hell, they hadn't even talked on the phone just to catch up. It wasn't very Jess. And since Paris was known to barge in at any time, she knew better than to try. But Paris was gone with Doyle for the weekend. No interruptions. She took a deep breath, trying to get her breathing evening, and answered.

"Hi," she said, trying to sound normal but her voice was low and cracked just the slightest bit.

"Hey," he chuckled. His voice was low and husky. Huskier than she had ever remembered it being. There was a slight pause in conversation before he continued. "Sorry, I never asked, is this okay?"

Rory had to bite her lip to stop from groaning at his concern. Somehow it was hot. "No, it's- it's fine," she stumbled. "I wouldn't've answered if it wasn't. Just," she let out a shaky sight, "Please, Jess, don't stop. I'm so close. I need this."

Without missing a beat, he jumped right in. "God that photo was so fucking hot, Rory. I want to put my dick in between your tits and fuck 'em."

Rory moaned. "I can't believe you told me to stop touching myself until I sent it to you. That was so hot."

"Mm, did you listen to me, baby? Did you do as I said? Were you a good girl for me?" His voice got rougher in her ear as he continued. She could hear how turned on he was.

"Of course I did, _sir._" She paused emphatically, knowing that he loved to have the control and power. And she loved giving it to him. She had stopped after all.

With a groan, he responded, "Good girl, baby. Yes, that's right, stop thinking for once and just listen to me make you feel good. Imagine me playing with your clit. Massaging it under my thumb, looking up at you. Are you playing with it?"

Rory nodded and panted, even though he couldn't see. He understood though and chuckled, "Yeah, that's right. Keep playing with it. I'd lick you top to bottom, only pausing to flick your clit with my tongue. Then I'd shove a finger in there. Did you do that for me?"

"Mmm-hmmm," came her long moan in response.

His answering growl forced him to keep quiet for a bit, and Rory swore she could make out the sound of him pumping himself up and down. For a minute, the pair just listened to the noises the other made.

"Fuck," Jess whispered under his breath.

"Hmm?" Rory questioned lazily, getting closer to her climax.

"I just love all the little noises you make. I wish I were there so I could hear them better."

There was a pause as the two kept pumping quicker, each getting closer.

"Rory, I'm close. I'm gonna-"

Rory cut him off. "Me too. Jess, I wanna watch you cum for me. Can we video chat?"

Jess let out a loud moan that time. "Fuck, Rory, yeah okay."

Within seconds, Jess's video request was coming through and Rory accepted. Suddenly, the pair were staring at each other's flushed faces. Both of them quieted in surprise, not having thought of this possibility. Yet, they both kept playing with themselves. Slowly, smiles came to their faces.

Jess was the first to talk. "Long time no see, gorgeous."

Rory's face got pinker from the blush that painted her face, but she didn't back down. "Hey handsome."

It was a familiar exchange between the pair. A normal greeting from high school. Another pause followed before Rory broke it.

"You know, I could hear you stroking yourself over the phone call and I just, I just had to see. It was way too much of a tease."

Jess's smile grew, "You know, I knew I turned you on, but this is just too much, Gilmore."

Rory pouted, sticking her bruised lip out, "Please?"

Jess's eyes narrowed the slightest bit. "Please what?"

Rory moaned, and their conversation was charged again. "Sir. Please sir."

"Good girl," Jess said. Rory's head went back and her spine arched. Her hand shook slightly, moving down, allowing Jess to get a clear view of her tits. "Fuck," he swore under his breath. He switched his camera to show him pumping his dick fast again, watching Rory watch on in delight.

"I wish I could taste you cumming on my face, sweetheart. I'd love to lap up your orgasm while you sit on my face. Rubbing my nose against your clit while I spank you, like a slut." Jess's words became more of a growl the further he got in the sentence, and when he said slut, Rory's finger plunged in deeply and her back arched as she started to cum with Jess watching every moment of it. He egged her on.

"Yes, that's my good girl. My slut. Cum for me. Ah fuck yes, Rory. You're so fucking hot."

As Rory came down from her orgasm, shaking and panting, she returned the favor. "Fuck. Thank you Jess. Fuck. Come on, cum for me now. I want to see you cum. You know how much I love watching you."

Jess groaned and sped up. Rory imagined it was because he liked making sure she was satisfied. Rory loved hearing how heavy his breathing was and kept encouraging him until he came a couple minutes later. She loved knowing that she had turned him on so much.

It was quiet as they both came down from their highs, regrouping and panting. They both got up, murmuring a "be right back" as they cleaned themselves up. When they returned, they both had new clothes on and Jess had switched his camera back to his face.

Now that Rory had the ability to focus on something other than an orgasm, she realized the years had only made Jess more handsome. Sure, she had gathered that from his social media, but something about seeing him naturally, at night, post-orgasm, she saw it differently. She blamed it on the orgasm talking.

He smiled, "That was fun. We should do that again."

Rory blushed in response but hummed her agreement nonetheless. Jess chuckled at such a non-committal response.

"So, did you just call me for that?" Jess wondered.

Rory bit her lip in guilt, "Sorry."

"Please, don't be sorry. You have nothing to be sorry for. That was great for me."

Rory laughed. "You know, actually, I do have some news that I've been meaning to share with you, but I was waiting until it was all confirmed."

"Oh yeah? What's that?"

"Weeelll, I've actually got a couple of interviews-"

Jess jumped in, cutting her off, knowing how much of their sexting went to this particular stressor, "No way! Rory, that's amazing. I knew you would."

Rory started laughing wholeheartedly and shushing him, telling him to let her finish. He obliged. "They're in New York. One's with the New York Times, which, as you can probably guess, I'm really excited about, and then a couple of other smaller papers. One of them is actually putting me up in a hotel. So I'll be around for a few days and I was wondering, well wondering if you wanted to get together at some point."

Jess's grin was melting even through a screen. She could see how proud he was. "Yes, absolutely. Let me know when and I'll clear my schedule. It'd be great to see you."

Rory's smile, whether or not she knew it, matched his. "Yeah, it'd be really nice to see you. I've missed you, Mariano."

"You too, Gilmore. Bed?"

"Yeah. Night, Jess."

"Sweet dreams, Rory."

Jess ended the call with a wink. As Rory drifted off to sleep, she was only slightly concerned about what an in person meeting between them would be like.

**A/N: I hope you enjoyed that. I'd love to read any and all reviews **


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